- Synthesis of Allylboranes via Cu(I)-Catalyzed B-H Insertion of Vinyldiazoacetates into Phosphine-Borane Adducts
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Cu(I) catalysts enable C-B bond formation via direct insertion of vinyldiazoacetates into B-H bonds of borane-phosphine Lewis adducts to form phosphine-protected allylboranes under mild conditions. The resulting allylborane-phosphine Lewis adducts can be used in the diastereoselective allylation of aldehydes directly without the need for removal of the phosphine. The allylation reaction proceeds with high diastereoselectivity and yields 5,6-disubstituted dihydropyranones after treatment with an appropriate acid.
- Drikermann, Denis,M??el, Robert S.,Al-Jammal, Walid K.,Vilotijevic, Ivan
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supporting information
p. 1091 - 1095
(2020/02/15)
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- Intramolecular Cyclization of Vinyldiazoacetates as a Versatile Route to Substituted Pyrazoles
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Vinyldiazo compounds undergo a thermal electrocyclization to form pyrazoles in yields of up to 95percent. The reactions are operationally simple, use readily available starting materials, require no intervention of a catalyst, and enable the synthesis of mono-, di- A nd tri-substituted pyrazoles. With the ability to produce highly substituted pyrazoles and the flexibility in installing various types of substituents, this method constitutes a new entry to this valuable heterocyclic scaffold and may be of interest to all branches of the chemical industry.
- Drikermann, Denis,G?rls, Helmar,Kerndl, Valerie,Vilotijevic, Ivan
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supporting information
p. 1158 - 1162
(2020/07/20)
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- Synthesis of pyridines by carbenoid-mediated ring opening of 2H-azirines
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Roaming the range: The title reaction tolerates a wide range of substituents on the resulting pyridine ring using mild reaction conditions (see scheme; esp=α,α,α′,α′-tetramethyl-1,3- benzenedipropionic acid). The formation of the key intermediate is catal
- Loy, Nicole S. Y.,Singh, Alok,Xu, Xianxiu,Park, Cheol-Min
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supporting information
p. 2212 - 2216
(2013/04/10)
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- Enantioselective reactions of donor/acceptor carbenoids derived from α-aryl-α-diazoketones
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The reaction of a variety of α-aryl-α-diazo ketones with activated olefins, catalyzed by the adamantyl glycine-derived dirhodium complex Rh2(S-PTAD)4, generates cyclopropyl ketones with high diastereoselectivity (up to >95:5 dr) and enantioselectivity (up to 98% ee). Intermolecular C-H functionalization of 1,4-cyclohexadiene by means of carbenoid-induced C-H insertion was also possible with this type of carbenoid.
- Denton, Justin R.,Davies, Huw M. L.
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supporting information; experimental part
p. 787 - 790
(2009/09/06)
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- Rhodium(II)-vinylcarbenoid insertion into the Si - H bond. A new stereospecific synthesis of allylsilanes
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Rh2(OAc)4 catalysed decomposition of vinyldiazocarbonyl compounds in the presence of organosilanes led stereospecifically to the corresponding allylsilanes in good yields. An asymmetric approach has also been considered as well as the extension of the methodology to the synthesis of other allylic systems.
- Landais, Yannick,Planchenault, Denis,Weber, Valery
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p. 9549 - 9552
(2007/10/02)
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- Stereoselective Synthesis of Seven-Membered Carbocycles by a Tandem Cyclopropanation/Cope Rearrangement between Rhodium(II)-Stabilized Vinylcarbenoids and Dienes
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Rhodium(II)-catalyzed decomposition of vinyldiazomethanes in the presence of dienes generated 1,4-cycloheptadienes by a tandem cyclopropanation/Cope rearrangement.Excellent stereocontrol of up to three stereogenic centers in the cycloheptadienes was achie
- Davies, Huw M. L.,Clark, T. Jeffrey,Smith, H. David
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p. 3817 - 3824
(2007/10/02)
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